Questions to Ask Before You Sign Anything

A Mobile restaurant owner signed a five-year equipment lease for a POS system. The salesperson said it was "flexible" and "easy to get out of if you need to."

Three years in, the restaurant changed owners. The new owner didn't want the system. The lease said it was non-transferable without a $15,000 buyout. The old owner was personally liable for $40,000 in remaining payments.

The salesperson was wrong. The contract was not flexible. The contract was the actual agreement.

Why these questions matter

Contracts are written to protect the party who drafted them. The vendor's contract protects the vendor. Your signature agrees to their terms.

That doesn't mean every contract is bad. It means you need to understand what you're agreeing to before you sign.

The questions below reveal problems that exist in every contract. The goal isn't to find a perfect contract—those don't exist. The goal is to find a contract whose problems you can live with.

Ownership and exit questions

These are the most important. Ask them first.

"Who owns the credentials and documentation for our systems?"

You need to own your own systems. If the vendor holds your admin passwords, domain registrar, and backup encryption keys, you're dependent on them for everything.

The answer should be: "You do. We maintain it for you, but you own access."

"What happens if we want to cancel? Walk me through the process."

Listen carefully to the answer. Is it a simple process? Are there fees? What are the timelines?

If they say "we don't have many cancellations" or "our clients stay for years," that's not an answer. That's a deflection.

"If we leave, what happens to our data? How do we get it, and in what format?"

You should be able to export everything. Not "we'll send you a report"—actual data you can use.

Ask to see the data export process. Have them explain exactly what you'd receive.

"What are the contract terms, and how does auto-renewal work?"

Month-to-month? Annual? Three-year? Know what you're committing to.

Also: When does it auto-renew? How far in advance do you need to cancel? Some contracts require 90 days notice before renewal. Miss that window, and you're locked for another year.

Pricing and billing questions

"What's included in this price, and what would cost extra?"

Get specific examples. "Server monitoring is included. Additional server installation would be quoted separately."

Watch for vague promises like "everything you need." That's not a scope—it's a sales line.

"How often do prices change, and by how much?"

Some contracts have price escalators built in. "Annual increases of up to 10%" is common. Some don't have limits at all.

Ask for historical examples. "What's an example of a price increase you've implemented in the past two years?"

"What happens if we exceed the scope we've agreed to?"

If you need additional work, what's the process? Hourly billing? Fixed quotes? Approval required first?

Know how changes happen before you need to make them.

Support and service questions

"What are your response times for different severity levels?"

Critical system down? Should get a response in under an hour. General question? Could be next business day.

Get this in writing. "Response within 4 hours for critical issues, 8 hours for high priority, next business day for standard requests."

"Who actually handles our account?"

A salesperson sold you. But who's actually doing the work? What's their experience level? Will you talk to them directly?

Some MSPs sell contracts, then handle everything with a help desk in another city. That might be fine—or it might be terrible.

"What does your support actually include? What's out of scope?"

Security awareness training: included or extra? Printer setup: included or extra? User training: included or extra?

The answer affects your actual monthly cost more than the advertised price.

Problem resolution questions

"What happens if we have a dispute? How do we resolve disagreements?"

Most contracts have a dispute resolution clause. Often it requires mediation before litigation. Sometimes it requires arbitration in a specific location.

Know where disputes get resolved before you sign.

"What's your liability if you cause a problem? What are you responsible for?"

Most IT contracts limit vendor liability to the fees you've paid. If they cause a breach that costs you $500,000 in damages, and their liability cap is $50,000, you're exposed.

This isn't always negotiable for small contracts. But you should know what the cap is.

The questions most people don't ask

"Can I have my attorney review this before signing?"

Any vendor who pressures you to not have an attorney review the contract should be avoided.

"What's the contract version we're signing? Can I get a clean copy?"

Sometimes vendors send a "standard contract" with handwritten changes that aren't reflected in the final version. Get a clean final version.

"Has this contract changed in the past year? What changed?"

Vendors update contracts. You want to know if you're signing something that was just made more restrictive.

What it costs

Contract review: If you have an attorney review a standard IT contract, expect to pay $500-$2,000 depending on complexity.

Not reviewing: Could cost $10,000-$100,000+ depending on what goes wrong. A bad contract clause that locks you in for three years could cost far more than a legal review.

What can go wrong

You signed an auto-renewing contract without knowing it. You tried to cancel in December. The contract renewed in November. You're locked until next year.

You didn't read the liability clause. Their mistake cost you $80,000 in damages. Their liability cap was $12,000. You absorbed the rest.

The vendor went out of business. You had 90 days of service left on a prepaid contract. They're gone. You're starting from scratch.

Exit fees were buried in the contract. You thought you'd pay two months' fees to leave. The actual termination fee was six months.

Questions to copy/paste

• Who owns credentials and documentation for our systems?
• What's the cancellation process, timeline, and fees?
• What happens to our data if we leave, and in what format do we receive it?
• What's the contract term, and how does auto-renewal work?
• What's included in the base price, and what costs extra?
• How often do prices change, and is there a cap on increases?
• What are your response times for different severity levels?
• Who actually does the work on our account?
• What's your liability cap if you cause a problem?
• Can I have my attorney review this before signing?
• What would it cost us to exit in year one vs. year three?

The bottom line

Most contract problems are preventable. The vendor will tell you their contract is standard, fair, and won't be an issue. But you have to live with it—not them.

Take the contract seriously. Read it. Ask questions. Have someone review it if it's significant.

The time you spend before signing is far less than the time you'll spend living with a bad contract.